TBHP-promoted sequential radical silylation and aromatisation of aryl isonitriles with silanes

Chemical Communications

Volumn 50, Issue 74, 2014, Pages 10864-10867

  Wang, Lei ^a   Zhu, Hui ^a   Guo, Songjin ^a   Cheng, Jiang ^a   Yu, Jin Tao ^a  

^a CHANGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CARBONYL DERIVATIVE; FREE RADICAL; NITRILE; POLYCYCLIC AROMATIC HYDROCARBON; SILANE DERIVATIVE; TERT BUTYL HYDROPEROXIDE;

AROMATIZATION; ARTICLE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RADICAL REACTION; REACTION ANALYSIS; REACTION OPTIMIZATION; SCREENING; SILYLATION;

EID: 84906337459     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc04773g     Document Type: Article

References (58)

1. F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003 345 1077-1101
2. J. F. Hartwig, Acc. Chem. Res. 2012 45 864-873
3. S. E. Denmark and R. F. Sweis, Organosilicon Compounds in Cross-Coupling Reactions, in Metal-Catalyzed Cross-Coupling Reactions, ed. A. de Meijere and F. Diederich, Wiley-VCH Verlag GmbH, Weinheim, 2008, pp. 163-216
4. G. R. Jones, Y. Landais, Tetrahedron 1996 52 7599-7662
5. T. Hiyama, E. Shirakawa, Top. Curr. Chem. 2002 219 61-85
6. Z. Rappoport and Y. Apeloig, Wiley-VCH, New York, 2001, vol. 3
7. C. Zarate, R. Martin, J. Am. Chem. Soc. 2014 136 2236-2239
8. N. Iranpoor, H. Firouzabadi, R. Azadi, J. Organomet. Chem. 2010 695 887-890
9. A. Hamze, O. Provot, M. Alami, J.-D. Brion, Org. Lett. 2006 8 931-934
10. S. Lulinski, J. Serwatowski, J. Org. Chem. 2003 68 9384-9388
11. K. Nishide, T. Miyamoto, K. Kumar, S. I. Ohsugi, M. Node, Tetrahedron Lett. 2002 43 8569-8573
12. A. S. Manoso, C. Ahn, A. Soheili, C. J. Handy, R. Correira, W. M. Seganish, P. DeShong, J. Org. Chem. 2004 69 8305-8314
13. M. Schlosser, C. Heiss, Eur. J. Org. Chem. 2003 4618-4624
14. M. Oestreich, G. Auer, M. Keller, Eur. J. Org. Chem. 2005 184-195
15. C. Cheng, J. F. Hartwig, Science 2014 343 853-857
16. P. I. Djurovich, A. R. Dolich, D. H. Berry, J. Chem. Soc., Chem. Commun. 1994 1897-1898
17. H. Ihara, M. Suginome, J. Am. Chem. Soc. 2009 131 7502-7503
18. F. Kakiuchi, M. Matsumoto, K. Tsuchiya, K. Igi, T. Hayamizu, N. Chatani, S. Murai, J. Organomet. Chem. 2003 686 134-144
19. F. Kakiuchi, K. Tsuchiya, M. Matsumoto, E. Mizushima, N. Chatani, J. Am. Chem. Soc. 2004 126 12792-12793
20. N. Tsukada, J. F. Hartwig, J. Am. Chem. Soc. 2005 127 5022-5023
21. M. Murata, N. Fukuyama, J.-I. Wada, S. Watanabe, Y. Masuda, Chem. Lett. 2007 36 910-911
22. T. Ishiyama, K. Sato, Y. Nishio, N. Miyaura, Angew. Chem., Int. Ed. 2003 42 5346-5348
23. T. Ishiyama, K. Sato, Y. Nishio, T. Saiki, N. Miyaura, Chem. Commun. 2005 5065-5067
24. G. Choi, H. Tsurugi, K. Mashima, J. Am. Chem. Soc. 2013 135 13149-13161
25. E. M. Simmons, J. F. Hartwig, J. Am. Chem. Soc. 2010 132 17092-17095
26. T. Saiki, Y. Nishio, T. Ishiyama, N. Miyauya, Organometallics 2006 25 6068-6073
27. E. M. Simmons, J. F. Hartwig, Nature 2012 483 70-73
28. B. Lu, J. R. Falck, Angew. Chem., Int. Ed. 2008 47 7508-7510
29. J. Oyamada, M. Nishiura, Z. Hou, Angew. Chem., Int. Ed. 2011 50 10720-10723
30. H. F. T. Klare, M. Oestreich, J.-I. Ito, H. Nishiyama, Y. Ohki, K. Tatsumi, J. Am. Chem. Soc. 2011 133 3312-3315
31. B. Zhang, C. G. Daniliuc, A. Studer, Org. Lett. 2014 16 250-253
32. H. Jiang, Y. Cheng, R. Wang, M. Zheng, Y. Zhang, S. Yu, Angew. Chem., Int. Ed. 2013 52 13289-13292
33. J.-J. Cao, T.-H. Zhu, S.-Y. Wang, Z.-Y. Gu, X. Wang, S.-J. Ji, Chem. Commun. 2014 50 6439-6442
34. Q. Wang, X. Dong, T. Xiao, L. Zhou, Org. Lett. 2013 15 4846-4849
35. L. Gu, C. Jin, J. Liu, H. Ding, B. Fan, Chem. Commun. 2014 50 4643-4645
36. L. Wang, W. Sha, Q. Dai, X. Feng, W. Wu, H. Peng, B. Chen, J. Cheng, Org. Lett. 2014 16 2088-2091
37. C. Pan, J. Han, H. Zhang, C. Zhu, J. Org. Chem. 2014 79 5374-5378
38. D. Leifert, C. Gabriel, A. Studer, Org. Lett. 2013 15 6286-6289
39. Z. Xia, J. Huang, Y. He, J. Zhao, J. Lei, Q. Zhu, Org. Lett. 2014 16 2546-2549
40. Z. Li, F. Fan, J. Yang, Z.-Q. Liu, Org. Lett. 2014 16 3396-3399
41. J. Lui, C. Fan, H. Yin, C. Qin, G. Zhang, X. Zhang, H. Yi, A. Lei, Chem. Commun. 2014 50 2145-2147
42. Z. Li, F. Fan, J. Yang, Z.-Q. Liu, Org. Lett. 2014 16 3396-3399
43. W. Sha, J.-T. Yu, H. Yang, J. Cheng, Chem. Commun. 2014 50 9179-9181
44. T. Xiao, L. Li, G. Lin, Q. Wang, Z.-W. Mao, L. Zhou, Green Chem. 2014 16 2418-2421
45. Z.-Z. Zhu, T.-T. Wang, P. Bai, Z.-Z. Huang, Org. Biomol. Chem. 2014 12 5839-5842
46. Q. Dai, J.-T. Yu, X. Feng, Y. Jiang, H. Yang, J. Cheng, Adv. Synth. Catal. 2014 10.1002/adsc.201400660
47. B. Zhang, A. Studer, Org. Lett. 2014 10.1021/ol5018195
48. T. C. Johnstone, S. M. Alexander, W. Lin, S. J. Lippard, J. Am. Chem. Soc. 2014 136 116-118
49. S. Simeon, J. L. Rios, A. Villar, Pharmazie 1989 44 593-597
50. I. Slaninova, K. Pencikova, J. Urbanova, J. Slanina, E. Taborska, Phytochem. Rev. 2014 13 51-68
51. W. K. Brewster, D. E. Nichols, R. M. Riggs, D. M. Mottola, T. W. Lovenberg, M. H. Lewis, R. B. Mailman, J. Med. Chem. 1990 33 1756-1764
52. H. Chen, H. Long, X. Cui, J. Zhou, M. Xu, G. Yuan, J. Am. Chem. Soc. 2014 136 2583-2591
53. T. Nakanishi, T. Suzuki, A. Saimoto, T. Kabasawa, J. Nat. Prod. 1999 62 864-867
54. L. Sripada, J. A. Teske, A. Deiters, Org. Biomol. Chem. 2008 6 263-265
55. O. B. Abdel-Halim, T. Morikawa, S. Ando, H. Matsuda, M. Yoshikawa, J. Nat. Prod. 2004 67 1119-1124
56. M. Tobisu, K. Koh, T. Furukawa, N. Chatani, Angew. Chem., Int. Ed. 2012 51 11363-11366
57. C. Chatgilialoglu, Chem. Rev. 1995 95 1229-1251
58. H. Zipse, Top. Curr. Chem. 2006 263 163-189